Totalsynthese von Steroiden. 1. Mitteilung. rac‐17β‐Hydroxydes‐A‐androst‐9‐en‐5‐on
- 1 November 1971
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 54 (7) , 2034-2042
- https://doi.org/10.1002/hlca.19710540734
Abstract
In connection with earlier work on the synthesis of 9β, 10α‐steroids, a new and practical synthesis of rac‐17α‐hydroxy‐des‐A‐androst‐9‐en‐5‐one (19) has been developed, based on a novel stereoselective condensation of 7‐hydroxy‐1‐nonen‐3‐one (3) with 2‐methyl‐cyclopentane‐1, 3‐dione (9) and subsequent transformations of the resulting tricyclic diene ether 12.Keywords
This publication has 13 references indexed in Scilit:
- Versuche zur Synthese von 9β, 10α‐Steroiden; B,C,D‐tricyclische VerbindungenHelvetica Chimica Acta, 1970
- Total synthesis of retroprogesteronesThe Journal of Organic Chemistry, 1968
- Des-A-pregnanes. Degradation of 11.alpha.-hydroxy-progesteroneThe Journal of Organic Chemistry, 1968
- A Nonphotolytic Synthesis of 10α- and 9β,10α-ProgesteroneJournal of the American Chemical Society, 1966
- Lactols Derived from Steroidal 17a-Oxa-D-homo LactonesThe Journal of Organic Chemistry, 1965
- Neuere Ergebnisse bei der Totalsynthese von SteroidenAngewandte Chemie, 1960
- Stereospecific Syntheses of trans-1β-Hydroxy-8-methyl-4,5-(4'-methoxybenzo)-hydrindane, trans-1β-Hydroxy-8-methyl-4,5-(3'-methyl-4'-methoxybenzo)- hydrindane and d,l-Equilenin Methyl EtherJournal of the American Chemical Society, 1956
- Addition of Hydrogen Bromide to trans-4-Heptenoic AcidJournal of the American Chemical Society, 1954
- Über Steroide. 112. Mitteilung. Über die Herstellung des Δ8,14‐1,7‐Dioxo‐8,11‐dimethyl‐dodecahydro‐phenanthrens. Totalsynthetische Versuche in der Steroidreihe IHelvetica Chimica Acta, 1953
- Ring-Chain Tautomerism of Hydroxy AldehydesJournal of the American Chemical Society, 1952